Holiday rentals with a pool in Naples

4.99 out of 5 average rating, 152 reviews

Pool House+Game Room, Moments to Beach & Downtown

Welcome to our Happy Place! This fully renovated Naples retreat sleeps 6 and blends modern comfort with family fun. Enjoy a bright open-plan living area, chef’s kitchen, and 3 bedrooms including a master with pool access. Step outside to your private screened oasis with heated pool, lounge seating, grill, canal and golf course views. The garage game room offers ping-pong foosball & arcade basketball. Just minutes to beaches, dining, and downtown, it’s the perfect getaway for relaxation and play.

4.97 out of 5 average rating, 108 reviews

A spacious private pool area features a heated pool and spa, enclosed by a screen for comfort. Lush greenery is visible through the arches, enhancing the serene setting. Modern lounge seating is positioned nearby, inviting relaxation and enjoyment.

Home in Palm River

Luxurious Naples Home. Heated Pool. Mins to Beach.

Have fun with the whole family at this stylish Naples Costal Paradise Home. Tropical Oasis within minutes to the beaches, restaurants, shopping, entertainment. Heated pool/spa no jets, Wi-Fi, big lanai with BBQ and more. House is a 3-bedroom, 2-bathrooms fully renovated in coastal contemporary style with tile floors, coastal art, big kitchen and more. King bed, queen bed, 2 full beds, big modular couch. House will comfortably sleep 6 adults plus children. It has all you need for great vacation.

5 out of 5 average rating, 12 reviews

Apartment in Naples

Lux Lakefront Resort | Beach 3 MIN Drive | 70"TVs

🌴Naples Coastal Escape🌴 “After several Airbnb visits this place definitely stands out among the rest…” Enjoy sunrises and sunsets in this remodeled, quiet, lavish lakefront oasis at Park Shore Resort. ☞Screened lanai w/lakeview+alfresco dining ☞Gourmet kitchen+Coffee bar+Wine fridge ☞Rainfall showerheads ☞Towel Warmer ☞Workspace desk ☞Cable TV TOP LOCATION ☀️ Clam Pass Beach->3min by car /~20min walk 🍹Mercato->9min car 💎 Old Naples/5th Ave->10min car 🛒 Fresh Market Grocery->10min walk

A serene beach scene captures a vibrant sunset, with hues of pink and orange reflected on the water's surface. Gentle waves lap at the shoreline, while soft sand stretches along the beach, interspersed with small scattered shells.

4.97 out of 5 average rating, 120 reviews

Magical Gateway in Naples FL

You'll fall in love with this tinny but magical place in the heart of Naples, modern open concept,high end finishes, a lot light, 2 BR queens beds, fine blinens, full bathroom with marble, enclosed pool, spacious back yard and a wood burning fire pit, 2 parking spaces just few steps from your front door. This place is near to all Naples has to offer, beautiful beaches, dining & nightlife, it is only 3km from the beach, 3 km from 5th ave in Old Naples and less than a mile from shopping centers.

A spacious screened-in lanai features a heated pool with a shallow area for children. Luxury chaise lounges are positioned near the pool, offering comfortable seating. The outdoor space is designed for relaxation and enjoyment, with clear views of the surrounding greenery.

4.94 out of 5 average rating, 146 reviews

LUXE Oasis | HTD Pool~10 min Beach+5th Ave• Crib

Welcome to Your Naples Getaway! Why our home is perfect for your vacation: 🏖️ Beaches Nearby – Just a quick 10–15 minute drive to Via Miramar and Lowdermilk Beach. 📍Prime Location – Nestled on a peaceful street only 7 minutes from the iconic 5th Avenue. 🏡 Resort-Style Comfort – Relax in our fully screened lanai featuring: • Heated private pool • Luxury chaise loungers • Outdoor TV • Gas grill for BBQ nights Unwind with a cocktail, take a sunset dip, or simply kick back under the stars!

The image showcases a bright, inviting pool area featuring clear blue water illuminated by string lights above, creating a relaxed atmosphere. Surrounding spaces include a cozy living room with comfortable seating and a spacious kitchen area with modern fixtures and finishes.

4.96 out of 5 average rating, 144 reviews

Coastal Getaway *Heated Pool *3 King Rooms

Tropical Oasis Downtown Naples 3 BD/2 BA full house w/ a HEATED pool, outdoor entertaining, BBQ grill, lanai seating/dining for 8, outdoor games, 2 living rooms w/ large TVs (main room has a 75" screen TV), master suite w/ ensuite bathroom & flatscreen TV, all 3 bedrooms have king beds. Close to downtown restaurants/shopping (9 min), beaches/Naples Pier (14 min). DOG POLICY: Only after owner's approval, a non-shedding small dog is allowed with $100 per dog non-refundable fee (2 dog maximum).

5 out of 5 average rating, 105 reviews

A heated pool is enclosed within a screened lanai, featuring a colorful beach ball floating on the water's surface. Sunlight filters through the mesh walls, illuminating the pool area and surrounding greenery, while lounge chairs are positioned nearby for relaxation.

Cottage in Naples Park

Beach House on pond w/ HEATED pool - sleeps 6

This secluded and beautiful beachside getaway is yours. Perfectly positioned easy access to white-sand beaches & fabulous shopping/dining/golfing/site seeing experiences of Naples. (2 bed 2 bath.) Gorgeous lakeview, (turtles/ducks incl.). HEATED POOL. Enjoy fresh coffee at sunrise from lanai watching swans take their morning swim or have a nightcap near shimmering moonlit pond. We warmly welcome you to rest, relax and stretch-out at this incredibly charming Beach*House cottage.

A private outdoor space features a saltwater pool and hot tub, surrounded by lush greenery. Comfortable seating arrangements include a fire pit and outdoor dining area, all sheltered under a screened enclosure, providing a tranquil setting for relaxation.

4.97 out of 5 average rating, 213 reviews

LUXE: Beach Home w/ Screened Pool & Spa, BBQ

This 2,000-square foot stunner has a pool, hot tub, two-car garage, three bedrooms and four bathrooms. There are bikes and beach accessories on site to take to the beach. Guest who is booking the reservation must be 26 years or older. There is a fee of $100/night per person for any guest over 7 in total up to a maximum of 9 guests. For example, if you have 8 guests, then the extra charge will be $100 per night. Please enter the exact number of guests before completing your booking.

A private outdoor pool area features a rectangular pool surrounded by a spacious deck. Eight blue lounge chairs are positioned around the pool, and a square spa is integrated into the design. A barbecue grill is situated nearby against a white privacy fence, with tropical plants adding greenery.

4.92 out of 5 average rating, 100 reviews

664 Naples Beach Paradise Private Pool & Spa

Welcome to 664 Naples Beach Paradise! A luxurious 2BD/2BA newly remodeled pool home; a short ride/walk to the famously soft, white sands of SWFL beaches. Perfect location in North Naples; just minutes to shopping, dining & entertainment. Bring your loved ones and enjoy a care free luxurious vacation on our welcoming property. Our staff is dedicated to provide and ensure a wonderful experience throughout your stay.

4.96 out of 5 average rating, 100 reviews

Beach! Heated Pool, Game Room, 2 Kings, 2 Suites

We are Super Hosts since 2018. You can see our history of reviews by navigating to my profile. The perfect home for a beach vacation just 3 minutes to the beach and 2 king beds. Every room in the house includes streaming TV even the outdoor lanai. A large chef's kitchen with an oversized island is great for entertaining. Bikes, towels, beach chairs, and toys are all included! Great house to enjoy the Florida sun.

A backyard oasis features a heated pool surrounded by tropical landscaping. Lounge chairs are arranged around the pool, and a pink inflatable float adds a pop of color. An umbrella shaded seating area is visible nearby, contributing to the inviting outdoor space.

4.96 out of 5 average rating, 184 reviews

529 Whispering Palms Oasis | Private Heated Pool

NEW HEATED POOL creates your backyard Oasis! This 3 Bedroom, 2 Bathroom spacious home will book up fast. Located in the popular Naples Park neighborhood this home is between 2 world class beaches, Vanderbilt Beach & Delnor Wiggins Pass Beach. Mercato Shopping & Dining District is just a a quick 5 minute drive & Downtown Naples is just 15 minutes. 2 bicycles available for you to be at the beach in 5 minutes.

An outdoor living space features a screened lanai overlooking a pool. Comfortable loungers are positioned around the pool. A dining table with multiple chairs is set under a ceiling fan, complemented by a large area rug. The scene is bathed in natural light.

4.98 out of 5 average rating, 131 reviews

Sunside House, 3/2 Pool Home in Gated Community

Prepare to be impressed as you enter this beautiful home in the sought-after Community of Briarwood. It certainly has the 'WOW' factor. The open aspect of this great-room floor plan, which flows out to a large, very private SW facing Patio and Pool area, makes this a perfect home for entertaining, family time or your golf time. You will love how light, bright and spotless this gorgeous home is. So much NEW.

Popular amenities for Naples rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 57 reviews

A spacious screened pool area is shown, featuring a heated saltwater pool with built-in bench seating. Lounge chairs are positioned along the edge, and a hammock is visible nearby. The outdoor dining area and sectional seating are included, with a 55" Smart TV situated to provide entertainment.

Home in Bonita Shores

Private Palm Oasis - Close to Beach

4.97 out of 5 average rating, 29 reviews

Home in Bonita Springs

Family Oasis | Heated Pool + Beach Gear, Kid Ready

A cozy living room features a blue couch and a light-colored armchair, complemented by a wooden coffee table. A large television is mounted on the wall. Natural light enters through three windows, surrounded by potted plants, enhancing the inviting ambiance.

4.91 out of 5 average rating, 134 reviews

Charming Heated Pool Villa - minutes from beach

5 out of 5 average rating, 9 reviews

New! Perfect Pool Paradise

The serene backyard features a heated in-ground pool surrounded by lush landscaping and a hot tub. A screened patio offers a dining table and lounge area with inviting cushions. The open concept kitchen and living space are visible, showcasing modern appliances and ample seating for relaxation.

4.97 out of 5 average rating, 98 reviews

Attention Naples Lovers! Entire Home w/Pool&HotTub

A charming turquoise home is surrounded by lush landscaping featuring palm trees and colorful flowers. In the foreground, a heated swimming pool is nestled within a paved area, accompanied by several lounge chairs positioned for relaxation and sunbathing.

5 out of 5 average rating, 24 reviews

Walk To Beach & Shops! New 4 Bdr Pool Heated

A heated pool area features relaxing lounge chairs partially submerged in the water, accompanied by a large white umbrella providing shade. The pool is surrounded by a spacious deck, framed by lush greenery and palm trees, with additional seating visible in the background.

4.98 out of 5 average rating, 107 reviews

Private Naples Oasis w/ Cart, Gym & Saltwater Pool

A covered patio area features a cozy seating arrangement with a dark sofa and a wooden dining table. A modern fire pit is situated at the center, complementing the views of a screened-in pool and surrounding greenery beyond the transparent enclosure.

4.93 out of 5 average rating, 40 reviews

Bella Villa Naples - 4BDR - Pool -Vanderbilt Beach

Condo rentals with a pool

The image captures a view of a sandy beach leading to a pier extending into the ocean. Waves can be seen crashing against the pier, while green foliage frames the foreground, enhancing the natural coastal scenery under a clear blue sky.

4.98 out of 5 average rating, 120 reviews

FUN AT THE BEACH

4.95 out of 5 average rating, 329 reviews

A spacious pool area is surrounded by lush palm trees and vibrant flowers. The water is calm, with small fountains creating gentle ripples. Loungers line the pool's edge, inviting relaxation under the sun. Sunlight reflects off the surface, enhancing the serene atmosphere.

Condo in Lely Resort

Lely Greenlinks Golf Resort Luxury Condo

4.97 out of 5 average rating, 141 reviews

A living area features a black leather sofa, accent chairs, and a flat-screen TV on a light-colored media console. Two framed botanical prints are displayed on a yellow wall, while large sliding glass doors provide sweeping views of the bay and natural light.

Condo in Punta Rassa

2nd Floor Beachfront Condo Sanibel Harbour

A cozy living area features a spacious light-colored sofa and two armchairs, complemented by a glass-topped coffee table. A ceiling fan provides airflow, while natural light pours in through large glass doors. A television is mounted on the wall, enhancing the room's functionality.

4.94 out of 5 average rating, 108 reviews

Lush tropical 1st floor getaway in Naples

4.94 out of 5 average rating, 142 reviews

An aerial view captures a sprawling landscape featuring residential areas interspersed with waterways. The horizon showcases the ocean, with buildings lining both sides of the main road. Lush greenery surrounds the area, providing a sense of tranquility and connectivity to nature.

Condo in Bonita Shores

Amazing Condo-1 mile from Bonita Beach

A spacious lanai features two vibrant green chairs and a small table, overlooking a tranquil body of water. Lush greenery and a wooden bridge are visible, creating a serene view that enhances the outdoor living experience.

4.9 out of 5 average rating, 117 reviews

Park Shore Resort258 Top Loc. View, Pool, Tennis +

A modern living area is highlighted by a white sectional sofa and a circular glass dining table surrounded by stylish white chairs. Large windows provide views of a tranquil outdoor space with greenery and water, complementing the bright interior decor.

4.92 out of 5 average rating, 133 reviews

Beautiful Pool 5m to the Beach Downtown & Shopping

A spacious living area features modern white armchairs positioned beside a stylish sofa. A table is set with decorative placements, and light enters through large sliding glass doors, framing views of lush greenery outside.

4.92 out of 5 average rating, 169 reviews

Park Shore Resort Modern Top Floor 2 Bed 2 Bath

Other holiday rentals with a pool

A private backyard features a heated in-ground pool and spa, surrounded by lush greenery. Four lounge chairs sit alongside the pool, inviting relaxation. A floating swan pool float adds a playful touch. The covered lanai offers shade and is perfect for outdoor gatherings.

5 out of 5 average rating, 39 reviews

Gulf Haven Hideaway: Naples 4BD Oasis - Pool + Spa

5 out of 5 average rating, 18 reviews

The Shell Tree House Naples

An outdoor balcony features a round dining table surrounded by several chairs, offering stunning views of the ocean and a glowing sunset. The serene atmosphere is enhanced by soft colors in the sky, while a small table stands beside a chair.

5 out of 5 average rating, 20 reviews

The Club at Naples Cay 1101

5 out of 5 average rating, 10 reviews

A spacious outdoor area is highlighted by a uniquely shaped pool surrounded by lounge chairs. Umbrellas provide shade over seating areas, and a dining table is visible in the background. Lush palm trees frame the scene under a clear blue sky.

Home in Vanderbilt Beach

Resort Style Tropical Oasis

A serene saltwater pool is featured within a screen-enclosed lanai, surrounded by lush greenery and palm trees. A spa is integrated beside the pool, while comfortable seating and a shaded umbrella complete the outdoor space, inviting relaxation under the blue sky.

4.97 out of 5 average rating, 35 reviews

Heated Pool & Spa, Near Beach, Naples Luxury Home

An open-concept living area features a spacious sectional sofa with decorative cushions. A dining table with elegant chairs is visible, along with a modern kitchen displaying dark cabinetry, stainless steel appliances, and a large island with bar seating. Ceiling fans and recessed lighting enhance the ambiance.

4.93 out of 5 average rating, 91 reviews

Naples Home-Min to beach,shops,dining. Heated Pool

Villa in Vanderbilt Beach

A serene outdoor area features a large swimming pool surrounded by palm trees and sun loungers. The backdrop showcases a two-story home with ample glass windows, allowing natural light to illuminate the interior. Soft colors in the sky hint at sunset.

4.84 out of 5 average rating, 25 reviews

Luxurious "Villa in the Hills"